Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof Vadapalli Chandrasekhar' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology-Kanpur Kanpur 208016 INDIA ; _publ_contact_author_email VC@IITK.AC.IN _publ_section_title ; A tubular architecture in a phosphorus based trihydrazide, {P(S)[N(Me)NH2]3} ; loop_ _publ_author_name 'Vadapalli Chandrasekhar' 'Ramachandran Azhakar' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 258303' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H15 N6 P S' _chemical_formula_weight 198.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P6(3) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 9.1213(6) _cell_length_b 9.1213(6) _cell_length_c 7.1103(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 512.31(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2404 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour colorless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.431 _exptl_absorpt_correction_type 'Bruker SADABS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3429 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.29 _reflns_number_total 834 _reflns_number_gt 815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628' _computing_cell_refinement 'Bruker SMART V5.628' _computing_data_reduction 'Bruker SAINT+ V6.45' _computing_structure_solution 'Bruker SAINT+ V6.45' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.0539P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(10) _refine_ls_number_reflns 834 _refine_ls_number_parameters 43 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.3333 0.6667 0.17752(7) 0.01205(13) Uani 1 3 d S . . S1 S 0.3333 0.6667 0.45290(5) 0.01680(15) Uani 1 3 d S . . N2 N 0.11836(14) 0.53718(13) -0.09468(17) 0.0195(2) Uani 1 1 d . . . N1 N 0.15545(12) 0.50733(13) 0.09204(16) 0.0153(2) Uani 1 1 d . . . C1 C 0.10742(17) 0.33238(15) 0.1359(2) 0.0221(3) Uani 1 1 d . . . H1A H -0.0154 0.2600 0.1229 0.033 Uiso 1 1 calc R . . H1B H 0.1409 0.3259 0.2653 0.033 Uiso 1 1 calc R . . H1C H 0.1646 0.2939 0.0489 0.033 Uiso 1 1 calc R . . H1 H 0.1600(19) 0.5004(18) -0.181(3) 0.019(4) Uiso 1 1 d . . . H2 H 0.012(3) 0.485(3) -0.098(3) 0.030(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01303(17) 0.01303(17) 0.0101(3) 0.000 0.000 0.00652(9) S1 0.0202(2) 0.0202(2) 0.0100(3) 0.000 0.000 0.01009(10) N2 0.0189(5) 0.0235(5) 0.0137(5) -0.0012(4) -0.0053(4) 0.0088(4) N1 0.0157(4) 0.0146(4) 0.0133(5) -0.0001(4) -0.0016(4) 0.0058(4) C1 0.0242(6) 0.0158(5) 0.0227(6) 0.0001(5) 0.0000(5) 0.0073(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.6601(10) 3_565 ? P1 N1 1.6602(10) 2_665 ? P1 N1 1.6602(10) . ? P1 S1 1.9580(6) . ? N2 N1 1.4294(15) . ? N1 C1 1.4617(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N1 107.40(5) 3_565 2_665 ? N1 P1 N1 107.40(5) 3_565 . ? N1 P1 N1 107.39(5) 2_665 . ? N1 P1 S1 111.47(4) 3_565 . ? N1 P1 S1 111.47(4) 2_665 . ? N1 P1 S1 111.48(4) . . ? N2 N1 C1 115.84(10) . . ? N2 N1 P1 113.21(8) . . ? C1 N1 P1 120.39(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.330 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041 #===END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 258304' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H15 N6 O P' _chemical_formula_weight 182.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.226(3) _cell_length_b 9.956(2) _cell_length_c 13.349(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1757.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type 'Bruker SADABS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10918 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2173 _reflns_number_gt 1981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628' _computing_cell_refinement 'Bruker SMART V5.628' _computing_data_reduction 'Bruker SAINT+ V6.45' _computing_structure_solution 'Bruker SHELXTL V6.14' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.7229P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2173 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.15292(2) 0.18963(3) 0.28930(2) 0.01022(12) Uani 1 1 d . . . O1 O 0.14856(7) 0.33851(10) 0.29504(7) 0.0149(2) Uani 1 1 d . . . N1 N 0.23236(8) 0.12549(10) 0.37106(8) 0.0131(2) Uani 1 1 d . . . N2 N 0.20508(9) 0.00741(11) 0.42515(9) 0.0158(2) Uani 1 1 d . . . N3 N 0.03961(8) 0.12369(11) 0.30787(8) 0.0132(2) Uani 1 1 d . . . N4 N 0.03567(9) -0.01709(11) 0.28564(9) 0.0167(2) Uani 1 1 d . . . N5 N 0.19437(8) 0.14385(10) 0.17669(8) 0.0132(2) Uani 1 1 d . . . N6 N 0.22296(9) 0.00611(11) 0.15793(9) 0.0169(2) Uani 1 1 d . . . C1 C 0.33850(10) 0.16406(14) 0.37299(12) 0.0178(3) Uani 1 1 d . . . C2 C -0.02359(11) 0.16937(15) 0.39100(11) 0.0192(3) Uani 1 1 d . . . C3 C 0.14383(12) 0.20089(15) 0.08927(11) 0.0210(3) Uani 1 1 d . . . H1 H 0.2222(13) 0.0234(16) 0.4882(14) 0.018(4) Uiso 1 1 d . . . H2 H 0.2449(14) -0.0594(18) 0.4053(13) 0.023(4) Uiso 1 1 d . . . H3 H 0.0495(13) -0.0615(18) 0.3421(14) 0.026(4) Uiso 1 1 d . . . H4 H -0.0261(16) -0.0394(19) 0.2670(15) 0.032(5) Uiso 1 1 d . . . H5 H 0.2747(16) -0.0170(19) 0.1986(14) 0.030(5) Uiso 1 1 d . . . H6 H 0.1707(14) -0.0430(18) 0.1758(13) 0.022(4) Uiso 1 1 d . . . H7 H 0.3489(13) 0.2411(19) 0.3254(16) 0.027(5) Uiso 1 1 d . . . H8 H 0.3574(14) 0.1962(19) 0.4344(16) 0.031(5) Uiso 1 1 d . . . H9 H 0.3813(14) 0.0950(19) 0.3580(14) 0.028(5) Uiso 1 1 d . . . H10 H -0.0129(13) 0.2624(17) 0.3990(13) 0.024(4) Uiso 1 1 d . . . H11 H -0.0955(14) 0.1509(17) 0.3731(14) 0.031(5) Uiso 1 1 d . . . H12 H -0.0080(14) 0.1207(17) 0.4508(14) 0.028(5) Uiso 1 1 d . . . H13 H 0.0875(13) 0.1457(16) 0.0672(13) 0.022(4) Uiso 1 1 d . . . H14 H 0.1228(15) 0.292(2) 0.1051(15) 0.035(5) Uiso 1 1 d . . . H15 H 0.1914(16) 0.203(2) 0.0358(15) 0.037(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01101(18) 0.01003(19) 0.00963(18) 0.00023(10) 0.00013(10) -0.00001(11) O1 0.0162(5) 0.0116(4) 0.0169(5) 0.0006(3) -0.0002(3) 0.0000(3) N1 0.0127(5) 0.0133(5) 0.0133(5) 0.0030(4) -0.0022(4) -0.0009(4) N2 0.0200(6) 0.0139(5) 0.0134(6) 0.0039(4) -0.0014(4) 0.0012(4) N3 0.0131(5) 0.0121(5) 0.0143(5) -0.0014(4) 0.0013(4) -0.0016(4) N4 0.0180(6) 0.0119(5) 0.0203(6) -0.0006(4) -0.0020(4) -0.0040(4) N5 0.0167(5) 0.0122(5) 0.0109(5) 0.0004(4) 0.0006(4) 0.0030(4) N6 0.0214(6) 0.0134(5) 0.0159(6) -0.0012(4) 0.0000(4) 0.0040(4) C1 0.0126(6) 0.0171(6) 0.0237(7) -0.0026(6) -0.0032(5) -0.0008(5) C2 0.0168(7) 0.0228(7) 0.0180(7) -0.0030(5) 0.0050(5) -0.0016(5) C3 0.0308(8) 0.0198(7) 0.0123(7) 0.0026(5) -0.0015(5) 0.0069(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4853(10) . ? P1 N1 1.6441(11) . ? P1 N3 1.6550(11) . ? P1 N5 1.6636(11) . ? N1 N2 1.4259(14) . ? N1 C1 1.4556(16) . ? N3 N4 1.4336(15) . ? N3 C2 1.4618(17) . ? N5 N6 1.4444(14) . ? N5 C3 1.4599(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 N1 112.22(5) . . ? O1 P1 N3 110.67(5) . . ? N1 P1 N3 108.98(6) . . ? O1 P1 N5 109.44(5) . . ? N1 P1 N5 106.43(6) . . ? N3 P1 N5 108.97(5) . . ? N2 N1 C1 116.90(10) . . ? N2 N1 P1 119.65(8) . . ? C1 N1 P1 121.70(9) . . ? N4 N3 C2 116.13(10) . . ? N4 N3 P1 112.94(8) . . ? C2 N3 P1 120.54(9) . . ? N6 N5 C3 110.52(10) . . ? N6 N5 P1 120.21(8) . . ? C3 N5 P1 117.70(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.609 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.068 #===END